Checking out Charming
by Hooking
Summary: Disclaimer: I do not own OUAT nor will i ever and this was written purely as fiction there is some Henry/ so please don't read if you feel uncomfortable with and if you are not over 18. also please PM me or leave a review if you liked i plan to update a new chapter every week.
1. Chapter 1

Chapter 1

When Mary Margaret gave henry the book she thought it was to be an innocent book of fairy tales. But that was where she was wrong when henry first got the book he was eight he loved reading the story but whenever he saw the drawings of charming with his chiselled jaw and muscles popping from his shirt he got a little hard he'd never felt like this so went on his mum's (Regina's) computer and found out all about masturbation

3 Years later

Henry was now living in Mary Margaret's house with Emma and David who he had realised was the same man as the Prince from the cum covered pages of his book. Emma had left with Mary to go shopping and Henry assumed David left with them so he reached under his bed and pulled out a box which contained the book and a series of photos henry had secretly taken of David whilst in the shower or from over the stall in granny's at some of the hot men in Storybrooke including David (all flaccid of course) which he called his "wank bank". He then lowered his trousers and began wanking his semi hard 5 inch member after some time he began to pant and moan in fact he was moaning so loud he failed to hear his grandfather climbing up the stairs he only noticed when the knob of his door twisted and in walked a shocked David

"Hey what are you up to?" David questioned trying to sound innocent as henry frantically struggled to cover his now 6 inch 11 year old boy cock

"Oh nothing just looking at some old pictures henry said, his heart pounding in his chest

"Oh what of"

"Nothing" henry interjected whilst cramming the photos back into his box. As he did this one slipped out of his hands and flew across the floor to David's feet when David picked it up he saw a picture of Robin stood up pissing whilst holding his respectable 5 inch flaccid cock. David was taken aback by this but felt himself start to 'grow' hot.

"How many of these have you taken henry?" David asked trying to stay composed. Henry knew the game was up when David sat on his bed next to him and he nervously handed David the box full of photos taped to the pages next to the drawings of the character all relatively the same, men from storybrooke stood pissing whilst unsuspectingly being photographed: Hook 7", Graham 6.5", Mr Gold magically 8" soft, Robin, Augustus 4.5" and David. When David turned to the page of him many photos popped out one of him under the table at granny's on karaoke night when he ripped his pants and was freeballing (he thought no one had noticed) him in the shower fully naked and him on his bed asleep after that night he got really drunk and woke up with his pants round his ankles. Then he noticed on the drawing of his face there it was a mark like a watermark but slightly sticky, was this Henry's cum? "What's this" he asked

"My collection it's just I think... I'm gay"

"Well that's ok henry I thought I was gay when I was about your age"

"Grandpa, I want you to have sex with me" henry blurted out

"Henry you're 11 I'm... illegal and anyway I'm your grandpa"

"Exactly why I want you to do it so I don't make a fool of myself and because I trust and love you"

David was surprised when henry said that and he didn't say anything just simply parted his legs and gave henry a look almost to say "I love you too"

Looked like Henry's dreams were about to come true.


	2. Chapter 2

Sorry it's been a year (literally) I had exams but I'm back and I'm ready, are you?  
Please review and pm if you have a request/ideas.

Henry dropped to his knees between Charmings legs. Charming looked down at his grandson as Henry unbuttoned the top of his fly and slowly pulled down Charming's zip. David felt the release of tension as his tight jeans were pulled to his ankles, Henry then placed two of his fingers in the waistband of David's black boxers and pulled them down. As soon as Henry removed the pants a semi hard 7"inch cock sprung up and slapped him across the cheek.

With one look up at his grandfather Henry took the head of the cock into his mouth. He loved the taste of David's cock he started by licking the top and slowly worked his way down untill he felt the wiry hair tickle his nose and he gagged. A small amount of precum leaked from the end of the monster into his mouth. Henry instantly swallowed the salty liquid giving a small moan as he did. David shuddered in pleasure as his own grandson worked up and down his cock sucking and humming. David let out a massive moan and Henry could feel his cock get harder in his mouth. He instantly stopped sucking and David cried out in a moan of frustration, he was so close, then Henry said, "can I sit on it?"

David was surprised even after sucking his now 11 inch thick monster Henry still wanted to ride it. "Ok I guess I can't say no now." David turned Henry round and spread his cheeks he leant in and started licking Henry's little boy ass. It tasted so good and David hummed into Henry's ass making Henry let out a huge groan in ecstacy"FUCK ME GRANDAD!" Henry was in so much pleasure then David stopped and he picked Henry up so he was stood on the bed in front of David.

"You lower yourself down ok? We'll take it at your pace." David slowly lowered his ass onto the head of his grandad's giant cock he managed to get the whole head into his ass and he let out a huge gasp. David moaned and grabbed on to Henry's waist in a sudden moment of shock David pulled Henry down onto 8 inches of his cock and Henry let out a huge scream he was in so much pain but then David said "just breath and relax it'll feel good in a minute."

After some time henry felt comfortable sitting on his grandads cock and lowered himself down untill he could fit all 11 thick inches into his ass. Henry began to bounce on David's cock and David screamed in pleasure as the 11 year old boys ass cluched his cock so tightly it was euphoric. All of a sudden David picked up Henry and turned him over so he was on all 4's on the bed whilst David stood behind him thrusting into his grandson. Henry felt the thrusts begin to pick up in pace and intensity as David became more excited. "Take it you dirty little slut. You love your grandads massive cock in your ass don't you." Henry was too stimulated to answer him he felt like he couldn't breathe because David's cock was pushing soo deep inside of the boy. David began to moan louder and louder and Henry felt the hardening of his cock. As David quickly pulled out of Henry he turned him round and shot hot sticky strings of cum all over his grandson's willing face. after his evacuation henry sucked the cum out of his limpening cock. Then david dropped to his knees and took the teenagers 6" cock into his mouth. This was Henry's first ever blowjob and he screamed so loudly in pleasure and after a couple blows and links from David's skilled tounge Henry came into David's mouth and David drank every drop.

As David took Henry's cock out his mouth they heard the door slam and Mary called up the stairs "hiya we're back"  
"Hiya honey" David called back down to her whilst frantically getting dressed "you'd better clean up henry" David instructed before disappearing around the door as Henry brought his sleeve to his face and wiped it. Henry then got dressed and decided to go down stairs. When he got there he saw Emma and hook and Mary and they chatted for a bit. "What were you two up to up there?" Mary asked Henry.

"Uhhhhh..." Henry replied racking his brain for any excuse but all he could thing about was the amazing fuck he just had with his own grandad!

"we were discussing what we should have for dinner" David interjected saving Henry from thinking of an excuse.  
"Yeah" Henry agreed "we thought we should make tacos." Henry smirked he had finally understood that moment a couple months ago.  
"Hey lad what's that on your cheek?" Hook asked leaning forward and rubbing his finger along he rush cheek picking up a white sticky substance on his finger.

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What will happen? You'll have to wait for chapter three I really do enjoy this story if you want more please show me some support review/PM me and also follow the story and show it some love.  
Thanks for reading  
XHKX


	3. Chapter 3

Both David and Henry held their breath as Killian slowly brought his finger to his lips and sucked the sticky fluid. "Oh I uh... had a yoghurt earlier " Henry said desperately hoping Hook would buy it. "I see" said Hook as Henry and David both breathed a sigh of relief.  
There was something slightly arousing about the fact that his step dad had just licked his grandads cum off his face. A seed grew in Henry's mind he was going to fuck his stepdad.

About a month went buy and Henry and David had not fucked Henry was getting really horny and every time killian came round he'd go up to his room and wank whilst listening to Killian's voice and imagining himself bent double with Killian behind him. On Tuesday Emma was busy all day looking after Pongo and asked Henry to pop down to Killian's ship to give him back a scarf he'd lent her. Henry happily obliged knowing he'd get to go and see his biggest crush.

He boarded Killian's ship headed towards his quarters as he came to the door he opened it and saw Killian stroking a huge cock sat behind the table with his head back and eyes closed moaning in ecstacy this gave Henry a plan. Henry quickly left the room shutting the door behind him he then knocked loudly he heard the shuffle inside the room before Killian said "yes come in." Henry entered the room and in front of him was Killian stood in the centre of the room with a large bulge clearly visible through his tight leather shorts.  
"Hi I was just dropping off the scarf, Emma said thanks" Henry said  
"Good lad" Hook replied  
"I'm really thirsty you don't have anything to drink do you?" Henry asked the captain  
"of course my boy" came the reply from the gentleman as he handed over a glass filled with water. As Henry went to take the water he "accidentally" deliberately threw the water at Hook which soaked his trousers. "Ahh shit!" Hook explained "I'll have to change these now" he said starting at Henry as if to say leave.  
"You can change now if you want" Henry said contently sitting on a barrel in the corner. Hook let out a frustrated sight but thought Henry was family it doesn't matter. As he unbuttoned his leather trousers and they dropped to the floor Henry saw Hook's magnificent butt with a hairy mist covering the cheeks Hook had perfectly toned cheeks and looked so sexy it was everything Henry had dreamed and more at that moment there was a knock on the door. This was going to be awkward if someone walked it on a naked Killian and Henry just sat watching. "Hide!" Killian whispered with a hint of worrying his voice as he turned to face his cabinet to put get seem trousers out Henry slid under the desk. Killian opened the cupboard and there was no trousers, he panicked what could he do.  
"Killian are you in there?" he heard David call  
"Yes just a second mate" he called out whilst trying to think of a solution. What was he to do? The idea sprang to him in an instant he quickly ran to the desk and sat down before tucking his legs underneath and hiding his naked bottom half from David. "Come in" he called to David who preceeded to enter the room. For Henry he had just hidden before he saw a naked pair of legs sit down in the chair and close him in to the area under the desk, he was sandwiched in between Killian's legs when he heard David enter the room. The two gentlemen were talking above Henry's head as he sat staring at his step dad's gorgeous hairy flaccid cock. Killian had a decent size for a soft cock and Henry was in heaven he thought if he was gonna get his chance it was now.  
Meanwhile  
"Hiya Killian you haven't seen Henry have you?"  
"No sorry I can't say I have" killian remarked which made him think he didn't actually know where Henry was.  
"Oh ok it's just Emma said he had come to give you a sc-"  
"Fff-uck" Killian moaned, he had found Henry, he didn't know how to react he had just felt the warm lips of his step sons mouth wrap around his now hardening cock. He couldn't tell David what was happening.  
"Are you ok Killian?" David asked as the pirate squirmed in front of him.  
"Yeah just remembered I need to go do something, sorry I haven't seen Henry." Killian stammered trying to keep his cool.  
"Ok sorry I'll see you later" David said before leaving.  
After a couple seconds Killian let out a huge moan before grabbing a half naked Henry from underneath the desk. "What the fuck was that!" he exclaimed "you could have got us into really bit trouble you little shit. I'm your stepdad you shouldn't do this its bad. And now you need to be punished" Killian said with provocative tone to his scentance. Henry grinned he couldn't wait.

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I hope you enjoyed I'll try to get a chapter out every week my plan for the next chapter is to go really hardcore with leather and bdsm style scenes do you guys want that or something more tame? Please review and pm if you have any ideas.  
Thanks  
XHKX


	4. Chapter 4

"punished?" Henry said curiously.

"yes" hook replied stroking his metal prosthetic with his fingers.

"what are you going to do to me?" Henry asked with a seductive undertone to his voice.

Hook, perched on his chair, lifted Henry up and removed his trousers. Henry was excited he thought Hook was about to fuck him just like he'd dreamed of. Hook layed Henry down accross his knee and raised his hand before firmly bringing it down upon Henry's hairless boy ass. Henry cried out as he felt the pain shoot across his behind his skin was glowing red from the hard beating Hook had just delivered. Hook was grinning ear to ear looking down at the boy he had just mamed with his hand. Henry let out a little giggle hoping that this would calm Hook however Hook became more enraged "this is punishment boy" said Hook and He pulled the boy's hair which made Henry let out a moan.

"you should call me daddy." the pirate said scraping his hook along Henry's small fragile spine. The sensation of his step fathers cold metal implement running down his back made him shudder. With tears running down his face Henry stood up.

"I'm sorry daddy I don't want to do this anymore" Henry remarked as he made his way across the captains quarters towards the door.

"where do you think you're going" Hook shouted as he lurched accross the room wrapping his arm around Henry's neck. Henry nearly choked as his step father's grasp grew tighter. Henry felt the tip of Hook's cold metal hook sliding up his leg towards his ass.

"No" Henry screamed as he felt the sharp tip trace his ring but it was too late. Hook rammed his hook into Henry's ass making henry gasp for air as the cold steel prodded around his insides.

"got to stretch you out before I fuck your brains out haven't we mate." Killian whispered in Henry's ear however Henry was already to overwhelmed to hear what hook had said. The hairy man worked his claw around Henry's intestines prodding and poking everywhere he went.

All of a sudden Henry let out a massive gasp as he hit his prostate with the tip of the metal spike.

"yes daddy" Henry cried in pleasure "more more please daddy more". With that Hook vibrated his hook inside Henry's ass. As soon as Henry was beginning to enjoy the experience he wipped his claw out of the boy's ass.

"I am your daddy and you will obey me, yes boy?" Hook commanded

"yes yes daddy yes" Henry said falling to the floor.

"Glad we're in agreement" said Hook said as he knelt down behind the boy's rear and Henry knew what was coming next. Hook placed his 8 inch thick rod by Henry's tight boy entrance and with no warning just like his hook he thrust right into Henry, The boy felt as the small curly black hair at the top of Hook's cock rubbed against his ass hole. Henry groaned in pain he cried as he thrust in and out of him, deeper deeper Hook went Henry didn't think it was possible he felt all 8 inches or so he thought but Hook was only 6 inches in.

"2 more inches to go mate" he said before thrusting deeper and deeper Henry, with tears running down his face, screamed out "yes daddy please daddy oh daddy"

Killian was enjoying his son's ass so much the tight cavity clenching around his thick pirate cock he couldn't help but let out a big deep moan. Realising what he was doing all of a sudden he reminded himself that he was punishing the boy not pleasuring him he raised his hand again and smacked Henry accross the ass cheeks bringing back that red colour that shone before. Henry screamed in pain but he was enjoying this experience very. much he liked Killian's style of sex was much more rough and careless, don't get him wrong, he enjoyed sucking off David, licking that big princely cock but there was nothing he enjoyed more than being shagged hard and dirty by a black leather pirate. Hook continued his thrusting his cock pulsating in the boy's ass until he felt that all too familiar tingle with one last massive thrust killian drove himself deep into the boy and filled him with his seed. Hot pumps of liquid filled the wrecked 11 year old's ass and as Killian unsheathed his now soaked meat dagger Henry's ass pumped the cum back out again. It trailed down the boys leg as he collapsed to the floor sprawled out in exhaustion.

Killian got up and made his way over to his desk from one of the drawers he removed a massive butt plug the size of a large fist and whist Henry wasnt looking rammed it into the boy's ass, which of course made Henry release one of his moans that made Killian so hot under the collar. Hook leaned down to Henry and whispered in his ear,

"this doesnt come out untill the next time we meet ok?" although it didn't require an answer Henry, exhausted, let out a muffled "yes sir" before making his way over to the pile of clothes he had left behind Killian's desk. He slid into his clothes once again, adjusting the butt plug to the comfiest position he could find, which in itself was not very nice. Henry then got up and made his way towards the door as he passed Hook he kissed him on the cheek and said

"see you later...daddy" before winking and strolling awkwardly his back towards his house. On his way home he decided to make a stop by grannies and as he sat down in the booth he remembered, quite painfully, that there was a bath plug in his ass so he made his way to the toilet readjust.

thank you so much sorry for it taking forever i hoped you enjoyed the next chapter is up to you i cam make its really watersports scat orientated or clean sex you choose also who might he meet in the toiled PM me names.


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